Novel orthohalogenation reaction. Synthesis of orthochloroarylamines from nitroarenes.

Ayyangar, N. R.; Kalkote, Uttam R.; Nikrad, P. V.

doi:10.1016/s0040-4039(00)87031-8

Cited by 12 publications

(4 citation statements)

References 4 publications

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“…Evidence points to the fact that the more asynchronous the reaction and the longer the ionic intermediate lifetime the more probable the para attack. On the other hand, treatment with thionyl chloride leads predominantly to ortho substitution ( 19 → 20 , Scheme ), , whereas DAST leads to para substitution . For interaction of N -siloxy- N -arylamines with organoaluminum reagents the ratio of substitution products in the ortho and para positions varied from 3.7:1 to 1:2.…”

Section: [1x]-rearrangements (X = 3 5 7) Of N-oxyenaminesmentioning

confidence: 99%

Rearrangement of N-Oxyenamines and Related Reactions

2014

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Section: [1x]-rearrangements (X = 3 5 7) Of N-oxyenaminesmentioning

confidence: 99%

Rearrangement of N-Oxyenamines and Related Reactions

2014

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“…Regiospecific chlorination of phenol, either ortho-or para-, can be achieved using 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dienone or 2,3,4,4,5,6hexachlorocyclohexa-2,5-dienone, re~pectively.~~ N-Phenylbenzo-and Nphenylaceto-hydroxamic acids react with thionyl chloride at low temperatures to give o -chloroaniline derivatives in good yield. 58 The reactions are presumed to involve intramolecular electrophilic attack.…”

Section: Meoy Sime3mentioning

confidence: 99%

Chapter 10. Aromatic compounds

HEANEY¹

1982

Annu. Rep. Prog. Chem., Sect. B

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The plenary lectures, presented at the fourth international symposium on the chemistry of novel aromatic compounds, have been published.' It is now apparent that the transition from bond equalization, an accepted criterion for an aromatic structure, to bond alternation will be gradual.* In borderline cases the degree of distortion will be small. Substitution by methyl groups does not appear to affect the magnetic anisotropy of the benzene nucleus. Despite some criticism large anisotropies in the molar susceptibilities are stil! used as a test for ar~maticity.~The possibility of cycloheptatriene-norcaradiene isomerization in the presence of an annelated cyclobutadiene has been investigated as a probe for the antiaromaticity of the latter sub-unit. The n.m.r. spectroscopic results are in favour of a significant negative resonance en erg^.^ The extent and pattern of .rr-electron delocalization in aromatic (and olefinic) aldehydes have been investigated using lanthanum-induced diamagnetic shifts in 13C n.m.r. ~p e c t r a . ~The free-radical 2,2,6,6-tetramethylpiperidin-l-oxyl has been used as a shift reagent and paramagnetic effects have been reported for a number of arenes.6The temperature dependence of 'H spin-lattice relaxation times has been used to determine the size of the rotational barriers in methyl-substituted tripty~enes.~ Barriers involving bridgehead methyls are significantly increased by a peri-methyl group. This suggests that a gear effect is probably absent. The ground-state energy in, for example, l-fluoro-9-(l-naphthyl)fluorene is higher than in the parent hydrocarbon and results in a lowering of the rotational energy barrier.' Restricted rotation at the 1,8-positions has been observed by differential scanning calorimetry in 1,8-di( 1 -na~hthyl)naphthalene.~ A series of papers report the results of further investigations on the conformational behaviour of benzo-derivatives of medium-sized ring systems by dynamic '

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“…With regard to the synthesis of chlorinated 3-pyridyl acetamides/carbamates, the transformation proceeds through rearrangement of chlorosulphite Id to Ie , the isomerization of which affords to the chlorinated pyridine derivative 3 (Scheme 2c). 25, 31 The lack of 6-chlorinated products and products arising from a reaction with other nucleophiles indicates that the chlorine transfer step is most likely an intramolecular process.…”

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confidence: 99%